A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones

Aimin Song; Xiaobing Wang; Kit Lam

doi:10.1016/S0040-4039(03)00108-4

A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones

Aimin Song, Xiaobing Wang, Kit Lam

Biochemistry and Molecular Medicine

Research output: Contribution to journal › Article › peer-review

151 Scopus citations

Abstract

Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

Original language	English (US)
Pages (from-to)	1755-1758
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	9
DOIs	https://doi.org/10.1016/S0040-4039(03)00108-4
State	Published - Feb 24 2003

Keywords

Coumarin-3-carboxylic acids
Knoevenagel condensation
Meldrum's acid

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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abstract = "Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.",

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T1 - A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones

AU - Song, Aimin

AU - Wang, Xiaobing

AU - Lam, Kit

PY - 2003/2/24

Y1 - 2003/2/24

N2 - Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

AB - Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.

KW - Coumarin-3-carboxylic acids

KW - Knoevenagel condensation

KW - Meldrum's acid

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JF - Tetrahedron Letters

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